Ethyl 2-oxo-2-phenylethyl malonate | 149815-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 2-oxo-2-phenylethyl malonate
• 英文别名: 1-O-ethyl 3-O-phenacyl propanedioate
• CAS: 149815-65-6
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: VEPUGNSDGDJUPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 2-oxo-2-phenylethyl malonate 在 4-乙酰氨基苯磺酰叠氮 、 三乙胺 作用下， 以 乙腈 为溶剂， 以46%的产率得到Ethyl 2-oxo-2-phenylethyl diazomalonate
  参考文献：
  名称：

  Stereo and electronic effects in the rhodium(II)-mediated synthesis of polycyclic lactones and lactams from .alpha.-diazo ester and amide precursors

  摘要：

  The rhodium(II) carboxylate catalyzed decomposition of several alpha-diazo esters and amides has been studied. A series of 5-keto-1-diazo acetates were prepared by acylation of alpha-hydroxy ketones using the (p-toluenesulfonyl)hydrazone of glyoxylic acid chloride. Treatment of these compounds with Rh(II) acetate afforded products derived from carbenoid insertion into solvent. When the hydrogen atom of the diazo carbon was replaced with an electron-withdrawing substituent, smooth cyclization occurred to produce a carbonyl ylide dipole which was subsequently trapped with different dipolarophiles. A series of N-alkyl-2-diazo-3-oxobutylamides, when treated with a catalytic quantity of rhodium(II) acetate, gave furo[3,4-c]furans in good yield. The reaction proceeds via addition of a rhodium-stabilized carbenoid onto the acetylenic pi-bond to give a vinyl carbenoid which subsequently cyclizes onto the neighboring carbonyl group to produce the furan ring. N-Alkynyl-substituted 2-diazoacetamides were also found to cyclize onto the tethered alkyne unit. The resulting rhodium carbenoid can undergo intramolecular and bimolecular cyclopropanation depending on both electronic and conformational factors. Rotamer population of the starting diazoamide was also found to influence product distribution.

  DOI：

  10.1021/jo00069a030
• 作为产物：
  描述：

  丙二酸单乙酯 、 2-溴苯乙酮 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以63%的产率得到Ethyl 2-oxo-2-phenylethyl malonate
  参考文献：
  名称：

  乙酸衍生物的苯甲酸酯及其在2-氧代-4-苯基-5-（苯基肼基）-2,5-二氢呋喃-3-衍生物的合成中的应用

  摘要：

  研究了各种取代的乙酸苯甲酰乙酸酯1和重氮盐3的偶联。如果苯甲酰甲基乙酸盐是由一个electronaceptor基团如CN或COOEt烷基取代的3-取代的苯基-5-（苯基-亚肼基）-5- ħ -呋喃-2-酮4形成。还描述了氮杂和二氮杂类似物的合成。使用MS和NMR光谱对化合物进行表征。

  DOI：

  10.1002/jhet.5570450529